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Synlett 2017; 28(14): 1828-1834
DOI: 10.1055/s-0036-1588982
DOI: 10.1055/s-0036-1588982
letter
FeCl3·6H2O-Catalyzed Tandem Alkylation–Hydrolysis Reaction of Chain α-Oxo Ketene Dithioacetals with Alcohols: Efficient Synthesis of α-Alkylated β-Oxo Thioesters
Supported by: We are grateful to the Fundamental Research Funds for the Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis (130028652)Supported by: the National Nature Science Foundation of China (20902010)
Supported by: Natural Science Foundation of Liaoning Province (201602002)
Supported by: and the Foundation of Liaoning Province Education Administration (L2015003)
Further Information
Publication History
Received: 31 January 2017
Accepted after revision: 05 March 2017
Publication Date:
11 April 2017 (online)


Abstract
A novel FeCl3·6H2O-catalyzed tandem Friedel–Crafts alkylation–hydrolysis reaction between chain α-oxo ketene dithioacetals and alcohols to afford α-alkylated β-oxo thioesters has been successfully developed. The reaction is efficient in the presence of catalyst loading as low as 30 mol% in MeCN at room temperature, and a wide variety of α-alkylated β-oxo thioesters are efficiently synthesized in good yields.
Key words
tandem reaction - ferric chloride - thioester - ketene dithioacetal - Friedel–Crafts alkylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588982.
- Supporting Information